<i>N</i>‐2‐Pyridinylmethyl‐<i>N′</i>‐arylmethyl‐diaminomaleonitriles: New Highly Selective Chromogenic Chemodosimeters for Copper(II)

Schwarze, Thomas; Kelling, Alexandra; Müller, Henrik Høeg; Trautmann, Michael; Klamroth, Tillmann; Baumann, Otto; Strauch, Peter; Holdt, Hans‐Jürgen

doi:10.1002/chem.201201731

Cited by 16 publications

(21 citation statements)

References 23 publications

(14 reference statements)

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“…The new NHC precursor 1‐benzyl‐4,5‐dicyano‐2‐(pentafluorophenyl)‐3‐picolylimidazoline ( 5 ) was prepared in a facile five‐step synthesis. We started with the formation of the known N ‐benzyl‐ N′ ‐picolyldiaminomaleonitrile ( 4 )12 and the synthetic procedure was concluded with the condensation of 4 with pentafluorobenzaldehyde in glacial acetic acid to obtain 5 in a yield of 67 % (Scheme ). Thermogravimetric analysis (TGA‐MS) and differential thermoanalysis (DTA) were used to investigate the thermal decomposition and carbene formation of imidazoline 5 (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

“…[17] Compounds 1, [11] 4, [12] [PdCl 2 (PPh 3 For all manipulations, solvents were dried according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

“…We started with the formation of the known N-benzyl-NЈ-picolyldiaminomaleonitrile (4) [12] and the synthetic procedure was concluded with the condensation of 4 with pentafluorobenzaldehyde in glacial acetic acid to obtain 5 in a yield of 67 % (Scheme 3). We started with the formation of the known N-benzyl-NЈ-picolyldiaminomaleonitrile (4) [12] and the synthetic procedure was concluded with the condensation of 4 with pentafluorobenzaldehyde in glacial acetic acid to obtain 5 in a yield of 67 % (Scheme 3).…”

Section: Synthesesmentioning

confidence: 99%

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Efficient Palladium(II) Precatalysts Bearing 4,5‐Dicyanoimidazol‐2‐ylidene for the Mizoroki–Heck Reaction

et al. 2014

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The new N-heterocyclic carbene (NHC) complex [PdCl 2 {(CN) 2 IMes}(PPh 3 )] (2) ({(CN) 2 IMes}: 4,5-dicyano-1,3dimesitylimidazol-2-ylidene) and the NHC palladacycle [PdCl(dmba){(CN) 2 IMes}] (3) (dmba: N,N-dimethylbenzylamine) have been synthesized by thermolysis of 4,5-dicyano-1,3-dimesityl-2-(pentafluorophenyl)imidazoline (1) in the presence of suitable palladium(II) precursors. The acyclic complex 2 was formed by ligand exchange using the mononuclear precursor [PdCl 2 (PPh 3 ) 2 ] and the palladacycle 3 was formed by cleavage of the dinuclear chloro-bridged precursor [Pd(μ-Cl)(dmba)] 2 . The new NHC precursor 1-benzyl-4,5dicyano-2-(pentafluorophenyl)-3-picolylimidazoline (5) was formed by condensation of pentafluorobenzaldehyde with Nbenzyl-NЈ-picolyldiaminomaleonitrile (4). The NHC palladacycle [PdCl 2 {(CN) 2 IBzPic}] (6) ({(CN) 2 IBzPic}: 1-benzyl-4,5dicyano-3-picolylimidazol-2-ylidene) was prepared by in situ [a] 2952 thermolysis of 5 in the presence of [PdCl 2 (PhCN) 2 ]. The three palladium(II) complexes were characterized by NMR and IR spectroscopy, mass spectrometry and elemental analysis. In addition, the molecular structures of 2 and 3 were determined by X-ray diffraction. The π-acidity of (CN) 2 IBzPic was compared with (CN) 2 IMes and perviously reported π-acidic imidazol-2-ylidenes by NBO analysis. The Mizoroki-Heck (MH) reactions of various aryl halides with n-butyl acrylate were performed in the presence of complexes 2, 3 and 6. The new precatalysts showed high activity in the MH reactions giving good-to-excellent product yields with 0.1 mol-% precatalyst. The nature of the catalytically active species of 2, 3 and 6 was investigated by poisoning experiments with mercury and transmission electron microscopy. It was found that palladium nanoparticles formed from the precatalysts were involved in the catalytic process.Scheme 2. Preparation of NHC palladium(II) complexes 2 and 3.

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Section: Resultsmentioning

confidence: 99%

“…[17] Compounds 1, [11] 4, [12] [PdCl 2 (PPh 3 For all manipulations, solvents were dried according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Section: Synthesesmentioning

confidence: 99%

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Efficient Palladium(II) Precatalysts Bearing 4,5‐Dicyanoimidazol‐2‐ylidene for the Mizoroki–Heck Reaction

et al. 2014

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“…Furthermore, the ligand was employed for the bioimaging experiment utilizing the HeLa cells through confocal fluorescence microscopic experiment. Schwarze et al 173 reported the N-2-pyridinylmethyl-N'-arylmethyldiaminomaleonitriles (109-111, Fig. Ko et al 140 described a coumarin-based fluorescent sensor iminocoumarin 70 (Fig.…”

Section: Bodipy Based Cu 2+ Sensormentioning

confidence: 99%

Optical sensor: a promising strategy for environmental and biomedical monitoring of ionic species

2015

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There is fast growing research on designing and improving the metal recognition methodologies in the ecosystems and biological media. The fluorescent based techniques proved a mile stones for non-invasive metal sensation and quantification in the multichannel environment. Metals as the natural components of Earth's crust are generally present in trace concentrations in the environmental samples where the humic substances have complexation affinity toward them. Iron, zinc and copper are the 1 st , 2 nd and 3 rd adequate elements indispensable to the body in trace playing the crucial roles in many biological processes. However, the unregulated amounts either as excess or deficient may exacerbate deterioration to the vital organs and triggered the progression of complications. Beside these three essential elements, mercury is widely considered to be one of the most hazardous pollutants and highly dangerous elements due to its recognized accumulative and toxic characters in the environment and the ecosystem. In the current scenario, we have tried to summarize the maximum amount of recently developed fluorescent signaling materials for the Cu 2+ , Fe 2+ / Fe 3+ , Zn 2+ and Hg 2+ . The spectral shifting in the molecules on metal chelation, mode of complexation and stoichiometries of resulting adducts have been discussed in detail. Furthermore, the molecules which have been reported as intracellular metal detector via bioimaging are specifically highlighted that might be useful for the design and development of cell viable and membrane permeable molecular probes in the future perspective.

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“…However, these probes show a lack of selectivity in the presence of Fe 3+ and Fe 2+ or sensing ability in aqueous solvent [31][32][33].…”

Section: Introductionmentioning

confidence: 98%

A colorimetric chemosensor for the sequential detection of copper(II) and cysteine

Lee

Shin

et al. 2015

Dyes and Pigments

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N‐2‐Pyridinylmethyl‐N′‐arylmethyl‐diaminomaleonitriles: New Highly Selective Chromogenic Chemodosimeters for Copper(II)

Abstract: Copper chemodosimeters: The copper(II)-promoted air oxidation of 1-3 to form 4-6 permits the highly selective colorimetric detection of Cu(2+) ions. The formation of copper(II) complexes of 4-6 proceeds rapidly, and the chemodosimeters 1-3 are viable at physiological pH.

Cited by 16 publications

References 23 publications

Efficient Palladium(II) Precatalysts Bearing 4,5‐Dicyanoimidazol‐2‐ylidene for the Mizoroki–Heck Reaction

Efficient Palladium(II) Precatalysts Bearing 4,5‐Dicyanoimidazol‐2‐ylidene for the Mizoroki–Heck Reaction

Optical sensor: a promising strategy for environmental and biomedical monitoring of ionic species

A colorimetric chemosensor for the sequential detection of copper(II) and cysteine

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